ozonolysis with orthoxylene gives 3 different products explain
explain why ozonolysis of orthoxylene gives three different products
Ozonolysis is a chemical reaction that involves the reaction of ozone (O3) with a compound, usually an unsaturated hydrocarbon. The reaction often occurs through a cycloaddition process, where the ozone molecule adds to the double bond of the unsaturated compound.
In the case of orthoxylene, which is an aromatic hydrocarbon with a double bond, ozonolysis leads to the formation of three different products. Let's break down the reaction step by step to understand how these products are formed.
Step 1: Initial Reaction
Orthoxylene reacts with ozone to form a molozonide intermediate. The double bond oxygen of the orthoxylene adds to one of the ozone molecules, while the remaining oxygen of the ozone forms a bond with the other carbon of the orthoxylene.
Step 2: Rearrangement
The molozonide intermediate undergoes a rearrangement known as a Criegee rearrangement. In this step, the oxygen attached to the second carbon of the orthoxylene migrates to the carbon attached to the first carbon of the orthoxylene. This rearrangement leads to the formation of a Criegee intermediate.
Step 3: Further Reactions
The Criegee intermediate can undergo three different reactions, each leading to a different product:
1. Reaction with Water: The Criegee intermediate can react with water (H2O) through a process called hydrolysis. This reaction cleaves the Criegee intermediate, resulting in the formation of a carbonyl compound (aldehyde or ketone) and a hydroxyl (OH) group.
2. Reaction with Dimethyl Sulfide (DMS): The Criegee intermediate can react with dimethyl sulfide (CH3-S-CH3) in a process known as the Criegee rearrangement. This reaction leads to the formation of a sulfonium salt.
3. Reaction with a Carbonyl Compound: The Criegee intermediate can react with a carbonyl compound, such as aldehydes or ketones, in a process called Criegee alkene ozonolysis. This reaction generates a variety of products, including carbonyl compounds, alcohols, and ketones.
Overall, the different products formed during ozonolysis of orthoxylene are a result of the various pathways that the Criegee intermediate can follow. Depending on the reaction conditions and the presence of other compounds, the relative amounts of these products may vary.